JPH08253448A - 複素環式置換基を有するオキシ−フエニル−（フエニル）グリシノールアミド - Google Patents

複素環式置換基を有するオキシ−フエニル−（フエニル）グリシノールアミド

Info

Publication number: JPH08253448A
Authority: JP; Japan
Prior art keywords: phenyl; carbon atoms; formula; straight; group
Prior art date: 1994-12-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP7339893A

Other languages

English (en)

Japanese (ja)

Inventor

Ulrich Dr Mueller

ウルリヒ・ミユラー

Richard Dr Connell

リチヤード・コンネル

Siegfried Goldmann

ジークフリート・ゴルトマン

Klaus-Helmut Mohrs

クラウス−ヘルムート・モールス

Siegfried Raddatz

ジークフリート・ラダツ

Michael Dr Matzke

ミヒヤエル・マツケ

Rudi Dr Gruetzmann

ルデイ・グリユツツマン

Martin Beuck

マルテイン・ボイク

Stefan Dr Wohlfeil

シユテフアン・ボールフアイル

Hilmar Dr Bischoff

ヒルマー・ビシヨフ

Dirk Dr Denzer

デイルク・デンツアー

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-12-09

Filing date

1995-12-05

Publication date

1996-10-01

1995-12-05 Application filed by Bayer AG filed Critical Bayer AG

1996-10-01 Publication of JPH08253448A publication Critical patent/JPH08253448A/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 66
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
239000003814 drug Substances 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 70
-1 quinolin-2-yl-methoxy Chemical group 0.000 claims description 50
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
150000002431 hydrogen Chemical class 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 14
QMXOFBXZEKTJIK-UHFFFAOYSA-N Glycinol Natural products C1=C(O)C=C2OCC3(O)C4=CC=C(O)C=C4OC3C2=C1 QMXOFBXZEKTJIK-UHFFFAOYSA-N 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
201000001320 Atherosclerosis Diseases 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 5
239000011261 inert gas Substances 0.000 claims description 5
MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
101150035983 str1 gene Proteins 0.000 claims description 3
230000003213 activating effect Effects 0.000 claims description 2
229940126601 medicinal product Drugs 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims 2
238000009472 formulation Methods 0.000 claims 1
230000000879 anti-atherosclerotic effect Effects 0.000 abstract description 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
239000000126 substance Substances 0.000 description 47
239000000460 chlorine Substances 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
238000004440 column chromatography Methods 0.000 description 18
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 18
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 17
210000002966 serum Anatomy 0.000 description 17
239000011734 sodium Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
229910052794 bromium Inorganic materials 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
229910052801 chlorine Inorganic materials 0.000 description 14
239000011737 fluorine Substances 0.000 description 14
229910052731 fluorine Inorganic materials 0.000 description 14
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
108010062497 VLDL Lipoproteins Proteins 0.000 description 11
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
102000006991 Apolipoprotein B-100 Human genes 0.000 description 8
108010008150 Apolipoprotein B-100 Proteins 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
239000000725 suspension Substances 0.000 description 8
150000003626 triacylglycerols Chemical class 0.000 description 8
241000700159 Rattus Species 0.000 description 7
239000002585 base Substances 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
239000012071 phase Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
235000011054 acetic acid Nutrition 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000002245 particle Substances 0.000 description 6
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238000005160 1H NMR spectroscopy Methods 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
102000004895 Lipoproteins Human genes 0.000 description 5
108090001030 Lipoproteins Proteins 0.000 description 5
230000037396 body weight Effects 0.000 description 5
125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000002883 imidazolyl group Chemical group 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
239000004006 olive oil Substances 0.000 description 5
125000000168 pyrrolyl group Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
208000008589 Obesity Diseases 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
208000029078 coronary artery disease Diseases 0.000 description 4
239000012043 crude product Substances 0.000 description 4
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
238000005259 measurement Methods 0.000 description 4
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230000008018 melting Effects 0.000 description 4
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UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 4
239000004033 plastic Substances 0.000 description 4
230000000291 postprandial effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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239000007858 starting material Substances 0.000 description 4
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239000003316 glycosidase inhibitor Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
208000006575 hypertriglyceridemia Diseases 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000010354 integration Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
VCMGMSHEPQENPE-UHFFFAOYSA-N ketamine hydrochloride Chemical compound [Cl-].C=1C=CC=C(Cl)C=1C1([NH2+]C)CCCCC1=O VCMGMSHEPQENPE-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008141 laxative Substances 0.000 description 1
230000002475 laxative effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
YAKUWANKCCMBRN-UHFFFAOYSA-N methyl 2-(2-fluoro-4-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C=C1F YAKUWANKCCMBRN-UHFFFAOYSA-N 0.000 description 1
WXOGXMQKSABBFZ-UHFFFAOYSA-N methyl 2-cyclononyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetate Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C(C(=O)OC)C1CCCCCCCC1 WXOGXMQKSABBFZ-UHFFFAOYSA-N 0.000 description 1
CBKKTMCMOPYVES-UHFFFAOYSA-N methyl 2-cyclopentyl-2-[3-(methanesulfonamido)-4-(quinolin-2-ylmethoxy)phenyl]acetate Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C(NS(C)(=O)=O)=CC=1C(C(=O)OC)C1CCCC1 CBKKTMCMOPYVES-UHFFFAOYSA-N 0.000 description 1
STRQKQNWCLGFDD-UHFFFAOYSA-N methyl 2-cyclopentyl-2-[3-[(4-methylphenyl)sulfonylamino]-4-(quinolin-2-ylmethoxy)phenyl]acetate Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C(NS(=O)(=O)C=2C=CC(C)=CC=2)=CC=1C(C(=O)OC)C1CCCC1 STRQKQNWCLGFDD-UHFFFAOYSA-N 0.000 description 1
KJILLGSYAQBEIA-UHFFFAOYSA-N methyl 2-cycloundecyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetate Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C(C(=O)OC)C1CCCCCCCCCC1 KJILLGSYAQBEIA-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
230000004089 microcirculation Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
238000012261 overproduction Methods 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
108040007629 peroxidase activity proteins Proteins 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
108010037401 tendamistate Proteins 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229960001729 voglibose Drugs 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Quinoline Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP7339893A 1994-12-09 1995-12-05 複素環式置換基を有するオキシ−フエニル−（フエニル）グリシノールアミド Pending JPH08253448A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4443891A DE4443891A1 (de)	1994-12-09	1994-12-09	Heterocyclisch substituierte Oxy-phenyl-(phenyl)glycinolamide
DE4443891.5		1994-12-09

Publications (1)

Publication Number	Publication Date
JPH08253448A true JPH08253448A (ja)	1996-10-01

Family

ID=6535394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7339893A Pending JPH08253448A (ja)	1994-12-09	1995-12-05	複素環式置換基を有するオキシ−フエニル−（フエニル）グリシノールアミド

Country Status (4)

Country	Link
US (2)	US5646162A (de)
EP (1)	EP0716082B1 (de)
JP (1)	JPH08253448A (de)
DE (2)	DE4443891A1 (de)

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JP2011507909A (ja) *	2007-12-20	2011-03-10	エンビボファーマシューティカルズインコーポレイテッド	四置換ベンゼン

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EP0802192A1 (de) *	1996-04-17	1997-10-22	Bayer Ag	Heterocyclisch-substituierte Phenylglycinolamide mit antiatherosklerotischer Wirkung und Verfahren zu ihrer Herstellung
DE19619950A1 (de)	1996-04-17	1997-10-23	Bayer Ag	Heterocyclisch-substituierte Phenylglycinolamide
DE19615263A1 (de) *	1996-04-18	1997-10-23	Bayer Ag	Benzyloxy-substituierte Phenylglycinolamide
DE19615262A1 (de) *	1996-04-18	1997-10-23	Bayer Ag	Heteroverknüpfte Phenylglycinolamide
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DE4112533A1 (de)	1991-04-17	1992-10-22	Bayer Ag	Verfahren zur herstellung von enantiomerenreinen substituierten (chinolin-2-yl-methoxy)phenyl-essigsaeuren
DE4128681A1 (de) *	1991-08-29	1993-03-04	Bayer Ag	Substituierte mandelsaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
DE4219765A1 (de) *	1992-06-17	1993-12-23	Bayer Ag	Substituierte (Benzothiazolyl- und Chinoxalyl-methoxy)phenylessigsäurederivate
DE4226519A1 (de)	1992-08-11	1994-02-17	Bayer Ag	3-Substituierte Chinolylmethoxy-phenylessigsäurederivate
DE4302956A1 (de) *	1993-02-03	1994-08-04	Bayer Ag	Substituierte Imidazo(4,5-b)pyridine und Benzimidazole
DE4401893A1 (de) *	1994-01-24	1995-07-27	Bayer Ag	Substituierte Arylharnstoffe

1994
- 1994-12-09 DE DE4443891A patent/DE4443891A1/de not_active Withdrawn
1995
- 1995-11-27 DE DE59509076T patent/DE59509076D1/de not_active Expired - Fee Related
- 1995-11-27 EP EP95118609A patent/EP0716082B1/de not_active Expired - Lifetime
- 1995-12-01 US US08/566,460 patent/US5646162A/en not_active Expired - Fee Related
- 1995-12-05 JP JP7339893A patent/JPH08253448A/ja active Pending
1997
- 1997-01-13 US US08/785,146 patent/US5691337A/en not_active Expired - Fee Related

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2006508016A (ja) *	2002-02-01	2006-03-09	ブリストル−マイヤーズ　スクイブ　カンパニー	カリウムチャネル機能のシクロアルキル阻害薬
JP2011507909A (ja) *	2007-12-20	2011-03-10	エンビボファーマシューティカルズインコーポレイテッド	四置換ベンゼン

Also Published As

Publication number	Publication date
EP0716082A1 (de)	1996-06-12
US5646162A (en)	1997-07-08
DE59509076D1 (de)	2001-04-12
US5691337A (en)	1997-11-25
EP0716082B1 (de)	2001-03-07
DE4443891A1 (de)	1996-06-13

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JPH08253448A - 複素環式置換基を有するオキシ−フエニル−（フエニル）グリシノールアミド - Google Patents

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